【结 构 式】 |
【分子编号】60619 【品名】9-aminothieno[3,2-c][1]benzothiepin-10(4H)-one 【CA登记号】 |
【 分 子 式 】C12H9NOS2 【 分 子 量 】247.3416 【元素组成】C 58.27% H 3.67% N 5.66% O 6.47% S 25.93% |
合成路线1
该中间体在本合成路线中的序号:(VIII)Alkylation of 3-aminothiophenol (II) with methyl 3-(bromomethyl)thiophene-2-carboxylate (I) provides thioether (III). After protection of the amino group of (III) as the corresponding acetamide (IV), its methyl ester group is hydrolyzed under alkaline conditions, to provide the carboxylic acid (V). Activation of acid (V) with trifluoroacetic anhydride, followed by cyclization in the presence of boron trifluoride etherate gives rise to a mixture of regioisomeric thienobenzothiepinones (VI) and (VII), which are separated by column chromatography. Acidic hydrolysis of the desired isomer (VII) provides amine (VIII). Acid chloride (X), prepared by chlorination of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (IX), is then condensed with amine (VIII) to furnish amide (XI). Finally, oxidation of the sulfide group of (XI) to the title sulfone is accomplished by treatment with m-chloroperbenzoic acid
【1】 Mimura, T.; Ogasa, T.; Mori, S.; Matsushita, T.; Imai, E. (Kyowa Hakko Kogyo Co., Ltd.); Preparation method of tricyclic cpds.. JP 2002053580 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 60612 | methyl 3-(bromomethyl)-2-thiophenecarboxylate | C7H7BrO2S | 详情 | 详情 | |
(II) | 60613 | 3-aminobenzenethiol; 3-aminophenylhydrosulfide | C6H7NS | 详情 | 详情 | |
(III) | 60614 | methyl 3-{[(3-aminophenyl)sulfanyl]methyl}-2-thiophenecarboxylate | C13H13NO2S2 | 详情 | 详情 | |
(IV) | 60615 | methyl 3-({[3-(acetylamino)phenyl]sulfanyl}methyl)-2-thiophenecarboxylate | C15H15NO3S2 | 详情 | 详情 | |
(V) | 60616 | 3-({[3-(acetylamino)phenyl]sulfanyl}methyl)-2-thiophenecarboxylic acid | C14H13NO3S2 | 详情 | 详情 | |
(VI) | 60617 | N-(10-oxo-4,10-dihydrothieno[3,2-c][1]benzothiepin-7-yl)acetamide | C14H11NO2S2 | 详情 | 详情 | |
(VII) | 60618 | N-(10-oxo-4,10-dihydrothieno[3,2-c][1]benzothiepin-9-yl)acetamide | C14H11NO2S2 | 详情 | 详情 | |
(VIII) | 60619 | 9-aminothieno[3,2-c][1]benzothiepin-10(4H)-one | C12H9NOS2 | 详情 | 详情 | |
(IX) | 34552 | trimethylsilyl (2R)-3,3,3-trifluoro-2-methyl-2-[(trimethylsilyl)oxy]propanoate | C10H21F3O3Si2 | 详情 | 详情 | |
(X) | 60620 | 3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl chloride | C4H4ClF3O2 | 详情 | 详情 | |
(XI) | 60621 | 3,3,3-trifluoro-2-hydroxy-2-methyl-N-(10-oxo-4,10-dihydrothieno[3,2-c][1]benzothiepin-9-yl)propanamide | C16H12F3NO3S2 | 详情 | 详情 |